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The Sugar Chronicles - My First Time

My Most Sordid Encounters as a Sugar Baby

By Laura WilliamsPublished 6 years ago 4 min read

Those girls who claim sugar babies don't have to have sex with their daddies? They are talking bullshit! 99.9% of these type of relationships are a sexual one and my experiences are no different. I won't talk about the boring details of when and why I decided to let older men pay me for sex, so let's just get into the dirty details that I know you are all here for. My first time with a sugar daddy is not overly graphic, but it's a situation where I lose control, which is something you should NEVER do as a sugar baby.

I chatted to a couple of guys online before I decided to meet up with George in real life. An Italian guy who was in the city for business, he was looking for a young girl he could take out for dinner, treat like a princess....and then fuck afterwards. He seemed pretty handsome from his pictures and I was more than happy to oblige. He was offering $1000 for the night. I'd made sure that he transferred the money earlier in the day, which is what I always do.

We met in the lobby of a VERY swanky restaurant, I was wearing a red cocktail dress (as requested by George), I had curled my long dark hair, which cascaded elegantly down my back. My makeup subtle but attractive, I definitely looked the part. He called out to me in the bar, "Rose" (I NEVER give my real name) and I turned to face him. He was much porkier than in his photos, his protruding belly was visible through his expensive suit. His features were simple, apart from piercing blue eyes that seemed to stare into my soul straight away. I felt his erection press against me as he kissed me on either cheek, bringing himself in close to me, his eagerness was apparent.

Dinner was awkward, I was new to this and felt pretty lied to based on how he looked. Still, I reminded myself this was a business transaction and nothing more. I ordered more wine than I should have and after lots of drinking, plus a little eating, he invited me to his hotel room above the restaurant. He kissed me immediately after entering the room, forcing his tongue into my mouth and pushing me against the wall, his hand finding my stockings underneath my dress. I thought about saying no, I signed up to be a sugar baby, not a hooker, but the alcohol took hold and I gave in right away.

I was not attracted to this man in the slightest and still I let him undress me. I stood in my red panties and bra, complete with black stockings as he looked me up and down like a piece of meat, licking his lips.

"Beautiful," he said, as he unbuttoned his shirt and removed his pants. We went over to the bed and I lay down.

"No, I want you on top" George breathed as he removed his boxers. A mediocre erection sprung out and I retrieved a condom from my bag.

"I'll pay you more if we can fuck without protection."

"How much?" I asked, my inhibitions drifting away as I thought of the bills I had accumulating at home.


"$1000 extra" I argued and he agreed.

He lay down on the bed and I removed my panties and bra, my slim body was now his to oggle and posses for the night.

I started to play with my clit to try and get SOME lubrication down there, but he grabbed me by the wrists, "Just sit on my cock baby."

I did as he said, lowering myself down onto him slowly, his clammy hands gripped my buttocks as I started easing myself up and down on top of him. I tried to zone myself far away as I rode his dick, but his over enthusiastic grunts made it difficult. Luckily, he didn't take long to finish "look me in the eye as I cum inside you," he said. So I did.

As I pushed my body down on his cock one final time, I felt him release. The feel of his warm semen inside me almost made me sick, he was only the second man to do that — the first of whom I was in a real relationship with. I instantly felt regret at my decision to have sex without a condom.

I got off him and instantly went to clean up.

"Now come and sleep with me baby," he smiled at me as I came back into the room, beads of sweat glistening his face.

Oh fuck! I couldn't even leave right away, he'd paid for the night. I got in bed next to him, he demanded I stay naked, and he curled his body up behind me the way familiar lovers do.


In the middle of the night, he requested a blowjob and without a word, I buried my head under the covers. This was something I was particularly good at. He hasn't showered since we had sex, so I could taste myself on him. I licked up and down his shaft but he quickly grabbed my head and pushed me down on him. Deep throat was fairly easy, due to the size of his penis, so I sucked him aggressively. When he was about to come, I pulled his cock out of my mouth and took his load on my tits.

I woke before him in the morning, left a short and polite note requesting he send me the extra $1000 and left.

I'm happy to say not all my sugar daddy encounters were like this one, but you can learn more about this in the next installment...


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